Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2002(16): 2383-2386
DOI: 10.1055/s-2002-35216
DOI: 10.1055/s-2002-35216
PAPER
© Georg Thieme Verlag Stuttgart · New York
Lithium Perchlorate Catalyzed Regioselective Ring Opening of Aziridines with Sodium Azide and Sodium Cyanide
Further Information
Received
30 April 2002
Publication Date:
04 November 2002 (online)
Publication History
Publication Date:
04 November 2002 (online)
![](https://www.thieme-connect.de/media/synthesis/200216/lookinside/thumbnails/10.1055-s-2002-35216-1.jpg)
Abstract
Aziridines react smoothly with sodium azide and sodium cyanide in the presence of catalytic amount of lithium perchlorate under essentially mild and neutral reaction conditions to afford the corresponding β-azido and β-cyanoamines in high yields with high regioselectivity.
Keywords
lithium perchlorate - aziridines - regioselective - β-azidoamines
-
1a
Tanner D. Angew. Chem., Int. Ed. Engl. 1994, 33: 599 -
1b
McCoull W.Davis FA. Synthesis 2000, 1347 -
2a
Dureault A.Tranchepain I.Depezay JC. J. Org. Chem. 1989, 54: 5324 -
2b
Tanner D.He HM. Tetrahedron 1992, 48: 6079 - 3
Hudlicky T.Luna H.Price JD.Rulin F. J. Org. Chem. 1990, 55: 4683 -
4a
Katritzky AR.Rees CW. In Comprehensive Heterocylic Chemistry Vol. 7: Pergamon Press; Oxford: 1984. p.47 -
4b
Kump JEG. In Comprehensive Organic Synthesis Vol 7:Trost BM.Fleming I. Pergamon Press; Oxford: 1991. p.469 -
5a
Reets MT.Jaeger R.Drewlies R.Hubel M. Angew. Chem., Int. Ed. Engl. 1991, 30: 103 -
5b
Balsells J.Walsh PJ. J. Org. Chem. 2000, 65: 5005 -
6a
Leung WH.Yu MT.Wu MC.Yeung LL. Tetrahedron Lett. 1996, 37: 891 -
6b
Fernandez M.Jacobsen EN. Org. Lett. 1999, 1: 1611 - 7
Ferraris D.Drury WJ.Cox C.Lectka T. J. Org. Chem. 1998, 63: 4568 - 8
Wu J.Hou XL.Dai LX. J. Org. Chem. 2000, 65: 1344 -
9a
Sankararaman S.Nesakumar JE. Eur. J. Org. Chem. 2000, 2003 -
9b
Aggarwal VK.Mereu A.Tarver GJ.McCague R. J. Org. Chem. 1998, 63: 7183 -
10a
Yadav JS.Reddy BVS.Murthy ChVSR.Kumar GM.Madan Ch. Synthesis 2001, 783 -
10b
Yadav JS.Reddy BVS.Srinivas R.Madhuri Ch.Ramalingam T. Synlett 2001, 240 -
10c
Yadav JS.Reddy BVS.Jothirmai B.Murthy MSR. Synlett 2002, 53